Basic information
- CAS
23942-99-6- Standard SMILES
COc1ccc(C(O)C2c3c(cc4c(c3OC)OCO4)CCN2C)c(CO)c1OC- InChIKey
BHLLOBXLOWXZDQ-UHFFFAOYSA-N- Molecular formula
- C22H27NO7
- Average molar mass
- 417.5 g/mol
- Monoisotopic mass
- 417.1787522
Overview
Narcotinediol has been reported in Papaver orientale and Papaver pseudo-orientale with data available.
Names & identifiers
- Preferred name
- alpha-Narcotinediol
- IUPAC
- [2-(hydroxymethyl)-3,4-dimethoxyphenyl]-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanol
- English name
- [S-(R*,S*)]-3,4-dimethoxy-alpha1-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-o-xylene-alpha,alpha'-diol
- Molecular formula
- C22H27NO7
- Molecular weight
- 417.45
Names & synonyms
alpha-NarcotinediolRefChem:915563Narcotinediol23942-99-6[2-(hydroxymethyl)-3,4-dimethoxyphenyl]-(4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanolMLS002920177(-)-alpha-NarcotinediolEINECS 245-946-7CHEMBL358914DTXSID30946765NSC132826NSC279531
Show more names
(-)-α-Narcotinediol(-)-α-Narcotinediol, CAS 23942-99-61,2-Benzenedimethanol, 3,4-dimethoxy-α1-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (α1S)-[S-(R*,S*)]-3,4-dimethoxy-alpha1-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-o-xylene-alpha,alpha'-diol
NSC 132826NSC 279531NSC-132826NSC-279531SMR001797774NS00050934(S-(R*,S*))-3,4-Dimethoxy-alpha1-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-o-xylene-alpha,alpha'-diol[2-(Hydroxymethyl)-3,4-dimethoxyphenyl](4-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methanol
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 89.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 6
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 566
Physicochemical properties
- Melting point
- 130 · 130-132 °C(Solv: ethyl acetate (141-78-6); ethyl ether (60-29-7))
- Boiling point
- 570.3 · 570.3±50.0 °C(Predicted)
- Density
- 1.3 · 1.300±0.06 g/cm3(Predicted)
- solubility
- soluble in Chloroform, Dichloromethane, Ethyl Acetate, Methanol
- form
- Solid
- pka
- 13.25 · 13.25±0.20(Predicted)
- color
- White
Chemistry & industry
Applications
Uses(-)-α-Narcotinediol is a Narcotine derivative, a noscapinoid class of microtubule binding compounds that alter microtubule dynamics without affecting tubulin polymer mass. Noscapinoids show great promise as chemotherapeutic agents for the treatment of human cancers. Unlike Narcotine, (-)-α-Narcotinediol deos not inhibit small-intestinal transport in rats.
Upstream & downstream products
Upstream raw materials
Suppliers5 total
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Related reactions
0 records
No reaction records under the current filter.
Compound notes
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